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CAS No. : | 29681-43-4 | MDL No. : | MFCD00956223 |
Formula : | C8H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OJDKENGKKYVJLY-UHFFFAOYSA-N |
M.W : | 167.16 | Pubchem ID : | 1519345 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 42.01 |
TPSA : | 48.42 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.6 cm/s |
Log Po/w (iLOGP) : | 1.85 |
Log Po/w (XLOGP3) : | 1.01 |
Log Po/w (WLOGP) : | 0.88 |
Log Po/w (MLOGP) : | 0.08 |
Log Po/w (SILICOS-IT) : | 1.19 |
Consensus Log Po/w : | 1.0 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.68 |
Solubility : | 3.45 mg/ml ; 0.0207 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.62 |
Solubility : | 4.05 mg/ml ; 0.0242 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.22 |
Solubility : | 1.0 mg/ml ; 0.00601 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.81 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | Stage #1: With thionyl chloride In water at 0℃; for 97 h; Reflux Stage #2: Reflux Stage #3: for 48 h; Reflux |
To a cooled (0 °C) solution of picolinic acid (5.0 g, 40.6 mmol) in SOCl2 (15 mL) was carefully added H2O (950 μL), and the mixture was refluxed for 1 hr. SOCl2 (15 mL) was added at rt and the mixture was refluxed for 2 days. SOCl2 (15 mL) was added at rt and the mixture was refluxed for further 2 days. After removal of the solution under reduced pressure, the residue was dissolved in MeOH (30 mL) and the mixture was refluxed overnight. A solution of NaOMe (4.4 g, 81.2 mmol) in MeOH (50 mL) was added and the mixture was refluxed for further 2 days. After removal the solvent under reduced pressure, the residue was dissolved in water and extracted with CHCl3. The extracts were dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on SiO2 (hexane :AcOEt = 1 : 1 → 1: 4 → 1 : 10) to give a solid. This material was washed with hexane-Et2O (1 : 1) to give 16 (1.8 g, 26 percent) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 60℃; for 36 h; | A solution of methyl 4-chloro-2-pyridinecarboxylate hydrochloride (2.0 g, 9.7 mmol) in MeOH (25 ml.) was stirred at 600C for 36 h. The MeOH was removed on the rotovap, and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated to generate the title compound of Step A as a white crystalline solid in quantitative yield (1.6 g, 9.7 mmol). 1H NMR (400 MHz, DMSO-d6j: δ 8.48 (d, 1 H, J = 5.7 Hz), 7.51 (d, 1 H, J = 2.8 Hz), 7.19 (dd, 1 H, J = 2.6 Hz, 5.7 Hz), 3.87 (s, 3H), and 3.84 (s, 3H). |
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